October 7, 2026
Transfer files with a call: OpenAI Dot carried out a task across two Macs
Mitchell Hashimoto asked Dot to transfer benchmark results and found the files on the right Mac when he returned to his desk.
Mitchell Hashimoto
@mitchellh
Just called Chungus (my OpenAI Dot) while picking up Mexican food and asked it to transfer last night's Rex benchmark results from my Mac Studio to my MacBook Pro via Tailscale. Got back to my desk—the files were already there. What a fucking time to be alive.
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Dot transferred overnight Rex benchmark results from a Mac Studio to a MacBook Pro via Tailscale. Hashimoto gave the instruction by voice while picking up Mexican food.
To transfer files via Taildrop, users select the files and destination device themselves. In this case, an AI agent received the same instruction over the phone and completed it before its owner returned. Dot works inside ChatGPT: there is no need to open a separate service to make a call.
How to assign a task. Open dots in ChatGPT on your computer, complete the introduction and connect the apps you need. You can create a Dot in the app or browser. Then open its profile in the ChatGPT app on the computer containing the files, select Computers → Your computer → Allow access and confirm access.
The phone button is in the conversation with Dot. During a call, you can specify the files and destination device, and the agent can continue working after the call ends. Dot connects directly to one personal computer, which must stay online with the ChatGPT app open.
To transfer files via Taildrop, install Tailscale on both devices and enable Send Files under General settings in the admin console. Transfers are available on all plans between your own devices. The command `tailscale file cp <files...> <target>:` sends files, while `tailscale file get <target-directory>` retrieves received files into the selected folder.
In the Standalone Tailscale client for macOS, enable command-line access through Settings → CLI integration → Show me how → Install Now. This integration requires macOS Ventura 13.0 or later.
What the subscription includes. Under OpenAI's terms dated Sep 29, the first Dot is included in Pro or Business Premium at no extra cost. Conversations with it do not count toward ChatGPT usage limits, while tasks it launches in Codex and ChatGPT Work count toward the limits of those AI tools.
According to the documentation as of Oct 7, Dots are gradually rolling out to adult users on Pro 100, Pro 200 and Pro 500 outside the EEA, the UK and Switzerland. Business Premium and Enterprise are rolling out worldwide; on Enterprise, an administrator enables the feature.
Work assigned to Dot can continue after the call ends.
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